InsurTech Geek Podcast

Jay Vinda, Global CISO and Cyber Risk Engineering Lead at Mosaic Insurance, joins host James Benham live at ITC 2026 to explore cyber risk engineering, the emerging risks surrounding AI, and how cybersecurity intelligence is changing insurance.

Jay grew up in London wanting to be a chef, studied mechanical engineering, and spent a couple of months in Peru building wind turbines for villages without electricity. A cybersecurity graduate scheme in 2016 was meant to last a couple of years; he stayed, earned a master's in information security while working, and spent about eight years protecting banks and government before moving into insurance. At Mosaic he protects the company as its CISO and helps its cyber underwriters assess every risk the way an attacker would.

In this episode:

• Why the person who buys a cyber policy and the CISO who knows what could go wrong are rarely in the same conversation, and how Jay bridges the two.

• How criminal marketplaces and ransomware operators made funding, not technical skill, the real barrier to cybercrime.

• Why generative AI erased the old phishing tells, and what the scams that work today look like: no urgency and no link.

• Why the basics still beat the shiny tools, and why so much "AI-powered" security is fluff.

• What frontier AI changes for defenders, from vulnerabilities that sat undetected for 26 years to a risk appetite far lower than a criminal's.

Key Quotes:

"Insurers have loads of data, but they're just not using it very well."

"Social engineering is still a very easy way to compromise a company."

"Our risk appetite on the defensive side is just a lot lower than a criminal's."

"Really, you don't need that much to be a criminal."

Chapters:

00:00 Cyber risk engineering and emerging AI risks, live at ITC 2026

00:24 First time in Vegas and the original attention hackers

02:09 Growing up in London and wanting to be a chef

05:25 Mechanical engineering and wind turbines in Peru

06:05 Falling into cybersecurity in 2016

10:06 When cyber stopped being a game and became a board issue

11:06 Insurance, the honeypot of data

12:10 From banks and government to insurance

13:08 What Mosaic does: Lloyd's syndicates and skin in the game

14:13 Two hats: CISO and cyber risk engineering lead

16:06 The disconnect between the CISO and the cyber insurance buyer

18:32 A criminal marketplace that runs like a business

19:57 Phishing written by AI and the end of the easy tells

21:21 No urgency, no link

22:59 "How would I hack Mosaic?" and synthetic voice attacks

24:49 What keeps Jay up at night: the basics

26:34 Moving goalposts: MFA, passkeys and biometrics

28:09 Frontier AI and 26-year-old vulnerabilities

29:29 People doing stupid things: the gift card scam

30:05 Using AI as a proactive pen tester

31:01 Why defenders adopt AI slower than attackers

31:59 The people pleaser problem and wrap up

🔗 Connect:

Jay Vinda: https://www.linkedin.com/in/jayvinda/

Mosaic Insurance: https://www.mosaicinsurance.com | https://www.linkedin.com/company/mosaic1609

👤 Host:

James Benham: https://www.linkedin.com/in/jbenham

🎙️ This episode is sponsored by Terra, the next-generation Workers' Comp and Commercial P&C Software.

Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/

📌 Find InsurTech Geek:

LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/

Twitter/X: https://twitter.com/InsurtechGeek

Instagram: https://www.instagram.com/insurtechgeek/

Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out! 🤓

David Fernandez, Chief Claims Officer at Kingstone Insurance, joins host James Benham to explore claims transformation, operational excellence, and why the team comes before the technology.

David fell into claims almost by accident: a broken-down car and a newspaper ad for a claims rep trainee job at Progressive, one that came with a company car, started an 18-year run there.

A decade at Liberty Mutual followed, then stops at Unum and Point32Health, and now three years as Chief Claims Officer at Kingstone Insurance, where he has helped lead the company's turnaround.

In this episode:
• Claims quality is a grind, not a project. It is won file by file, day after day, until it becomes how the team works, not something you launch and move past.

• Why "until you have a team that you believe in, you're swimming up river" is the foundation every other fix in a claims org sits on top of.

• How a small, empowered team rebuilt Kingstone's claims platform in four months, with clear ownership and not a single slide deck.

• Why making no decision is worse than making a suboptimal one, and how giving people room to admit mistakes keeps a transformation moving.

• Inside Kingstone's catastrophe playbook, built for a Northeast climate that delivered 11 declared catastrophes in the first quarter alone.

Key Quotes:
"We sell a piece of paper and a promise. Sometimes it's a PDF."

"Making no decision is worse than making a suboptimal decision."

"Until you have a team that you believe in, you are swimming up river."

"There was not a single slide for that whole thing."

🔗 Connect: David Fernandez, Kingstone Insurance links
👤 Host: James Benham
🎙️ Terra sponsor block + InsurTech Geek socials + standard sign-off (unchanged, copied from the standing footer)

Dawn Miller, Chief Commercial Officer of Lloyd's and CEO of Lloyd's Americas, joins host James Benham to explore what an insurance ecosystem actually is, why a 338-year-old market still has to fight to be understood, and how Lloyd's Lab turned an accelerator into a pipeline that keeps its alumni in the industry.

Dawn grew up in Georgia and went to university in Washington, D.C. planning to run the United Nations. Instead she found risk transfer — first at OPIC, now DFC, then political risk at Willis — and stayed for 25 years, through Chubb, AXA and AIG, with a detour building a company in Prague along the way. She joined Lloyd's for the transformation challenge: an institution with 338 years of legacy, a license network trading in 200 countries, and a purpose statement that needed a reset.

Recorded on site at InsurTech Insights New York 2026.

In this episode:

• What separates an ecosystem from a marketplace or a network — Dawn's answer is the heartbeat at the center, where you can watch value move between stakeholders

• Why Lloyd's reset its purpose statement in March, and why "global" appears in it twice when 60% of market premium comes out of North America

• The narrative problem: a coffee house origin story and 338 years are not enough to win capital and clients

• Inside Lloyd's Lab seven years on — two themed cohorts a year, structured problem statements, government partners, and the 95% of alumni still in insurance

• Why insurance should talk about itself as a resilience industry that happens to sell insurance, and what that reframe does for talent

Key Quotes:

"We bring together the world's leading risk-takers to advance global progress."

"Your competitor one day could be your partner the next, your client the following."

"We can't just say we started in a coffee house. We've been here 338 years. That's not enough."

"Ecosystem is the only word that gives a sense of a bit of a heartbeat to the center of it."

"Talk about us as a resilience industry that happens to sell insurance."

🔗 Connect:

Dawn Miller: https://www.linkedin.com/in/dawn-mmiller/

Lloyd's: https://www.lloyds.com | https://www.linkedin.com/company/lloyd%27s-of-london/

👤 Host:

James Benham: https://www.linkedin.com/in/jbenham

🎙️ This episode is sponsored by Terra, the next-generation Workers' Comp and Commercial P&C Software.

Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/

📌 Find InsurTech Geek:

LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/

Twitter/X: https://twitter.com/InsurtechGeek

Instagram: https://www.instagram.com/insurtechgeek/

Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out! 🤓

Ken Bunn, Vice President of Claims at Builders Mutual Insurance Company, joins hosts James Benham and Rob Galbraith to explore how a construction only Southeast insurer built its claims department from scratch, why the AI tools that stick are the ones adjusters never have to think about, and what it takes to keep training junior adjusters into seniors.Ken's path ran through 18 years at Nationwide, rotating between claims leadership, field training, and IT program management, before Builders Mutual asked him to build a claims department that didn't exist yet. Twelve years later, the company has grown from roughly 200 million to 650 million in revenue, and Ken still leads much of the original team he brought over from an outsourced TPA.In this episode:• Why Builders Mutual pulled its claims department in-house, and how they kept close to 30 of the original 40 people they brought over.

• The predictive AI models that worked exactly as designed and still failed to stick.

• The unglamorous automation, document routing, indexing, and med record summaries, that actually delivered the ROI.

• Ken's leadership philosophy for change management with no formal program at all.

• Why work comp rate softening may be hitting a floor as catastrophic claims costs climb. Key Quotes:"You can't work on an assembly line and do brain surgery at the same time."

"It's not going to solve all your problems. It's going to help."

"There might be something wrong when your claims adjusters are the happiest people in the room."

"Be real. Tell people what's going to happen and why you're doing it."

"Pick and choose your tools well so they inform the adjuster, not just replace them."🔗 Connect:Ken Bunn: https://www.linkedin.com/in/kenbunn/Builders Mutual Insurance Company: https://www.buildersmutual.com | https://www.linkedin.com/company/builders-mutual-insurance-company👤 Hosts:James Benham: https://www.linkedin.com/in/jbenhamRob Galbraith: https://www.linkedin.com/in/rob-galbraith/🎙️ This episode is sponsored by Terra, the next-generation Workers' Comp and Commercial P&C Software.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out! 🤓

Freddie Scarratt, Global Deputy Head of InsurTech at Gallagher Re, joins James Benham and Rob Galbraith to unpack why 95% of all insurtech funding in Q1 2026 flowed into AI-focused companies, and what that means for the birth of an entirely new risk class: AI liability. From the Air Canada chatbot case that made headlines, to the hard lesson the industry learned when cheap venture capital tried to scale insurtechs like SaaS businesses, Freddie brings a reinsurance broker's view of where AI liability, cyber, and professional indemnity are converging into one digital risk category, and why insurance, unlike every other industry, can never fully cap its downside.

Cyber risk is evolving faster than the policies written to cover it. Rick Wong, Head of Insurance at Parametrix Insurance, sits down with James Benham live at RIMS 2026 to talk about the future of parametric cyber — and why the standard tech E&O form wasn't designed for the exposures that actually matter today.

Parametrix is a Lloyd's coverholder writing parametric cyber, SLA, and enterprise risk. Named Cyber Underwriting Team of the Year at the Intelligent Insurer Awards, Q1 2026 already at 60% of full-year 2025 volume.

In this episode:
→ Why standard cyber policies fail data centers
→ How parametric products are being used as financial tools — not just risk transfer
→ AI-powered criminal organizations, nation-state actors, and what's coming in cyber threats
→ Building a differentiated MGA in a space with growing capacity and real opportunity

Guest: Rick Wong - Head of Insurance at Parametrix Insurance
Website: https://www.parametrixinsurance.com/
LinkedIn: https://www.linkedin.com/in/rick-b-wong/

Host: James Benham - Founder & CEO at JBKnowledge

Sponsor: Terra - Cloud-native Workers' Comp and P&C platform | terra.insure

Paul Andrews and Mark Elliott of PoloWorks join us to discuss how insurers can access,

operate, and scale across the Lloyd’s and broader insurance market. Drawing on decades of

experience across underwriting, reinsurance, and operations, they share how PoloWorks is

simplifying complexity through turnkey managing agency solutions, outsourced services, and

support across the full insurance lifecycle.

Danilo Raponi, Group Head of Innovation at Generali, joins us to discuss how one of the world’s largest insurers structures and scales innovation. From venture investments and startup partnerships to AI, IoT, and climate-focused solutions, Danilo shares how Generali is evolving insurance from a reactive claims payer to a proactive partner in risk prevention. 

Dr. Thomas Kuhnt, Chief Information Officer and Chief Operating Officer at HDI Global SE, joins hosts James Benham and Rob Galbraith to explore leading digital and AI transformation in corporate and specialty insurance — recorded live at Insurtech Insights London on March 18, 2026.

Dr. Kuhnt's path is unlike most in insurance. A PhD in algebraic number theory from the University of Illinois Urbana-Champaign, 15 years at McKinsey building the European insurance practice, and now a dual CIO/COO seat overseeing technology, operations, and transformation at one of the world's oldest and largest industrial insurers. He brings a systems thinker's lens to one of the most complex transformation challenges in the industry.

In this episode:

• Why organizations must stop waiting for perfect conditions and start experimenting with AI now

• How agentic AI is transforming input management and underwriting workflows at HDI Global

• Why business leads — not IT — should own AI transformation in global insurance organizations

• The process trap: how applying AI to broken workflows just accelerates the breaking

• What the next 5–10 years really looks like for underwriters and claims professionals at the desk level

Key Quotes:

"Don't wait. Start to experiment and iterate. This is not going to go away."

"Business becomes IT — and IT becomes business."

"We're overestimating the short-term impact — but underestimating it in the long term."

"Seventy to eighty percent of an underwriter's work is just rekeying data. That's not really underwriting."

"The first question should always be why — and that's an ops question, not a tech question."

🔗 Connect:

Dr. Thomas Kuhnt: https://www.linkedin.com/in/thomas-kuhnt/

HDI Global SE: https://www.hdi.global/ | https://www.linkedin.com/company/hdi-global/

👤 Hosts:

James Benham: https://www.linkedin.com/in/jbenham

Rob Galbraith: https://www.linkedin.com/in/rob-galbraith/

🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.

Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/

📌 Find InsurTech Geek:

LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/

Twitter/X: https://twitter.com/InsurtechGeek

Instagram: https://www.instagram.com/insurtechgeek/

Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Amir Kabir, Founding & Managing Partner at Overlook Ventures, joins hosts James Benham and Rob Galbraith to reimagine risk in the age of AI — what the last decade of insurtech got wrong, where the next wave of opportunity actually lives, and why "liability is getting weird" is an understatement.

Amir spent the first chapter of his career in Germany, building enterprise software at a Karlsruhe startup that was eventually acquired by a Silicon Valley company. In 2013 he immigrated to the US for an MBA at Georgetown, became the third person on the founding team at Munich Re Ventures, and helped grow that fund from $50M to over $1B. He later served as General Partner at AV8 Ventures leading the financial services practice before launching Overlook Ventures to invest full-time at the intersection of risk and frontier technology.

In this episode:

• Why the early insurtech era mistook insurance for a scalable SaaS business

• "Insurance is a get-rich-slowly business" — and what that means for exit math

• The Overlook thesis: investing in the infrastructure of risk across every tech cycle

• Where AI is real in insurance today (claims, underwriting data extraction) — and where regulation still slows it down

• The emerging risk categories that don't fit today's policy structures: autonomous systems, longevity, and reputational narrative risk

Key Quotes:

"Insurance is a get-rich-slowly business."

"Technology moves in cycles. Risk always evolves through them."

"Liability is getting weird."

"Try to find a problem before you find a solution."

"A brand can be destroyed in 48 hours by a viral moment."

🔗 Connect:

Amir Kabir: https://www.linkedin.com/in/amirkabir/

Overlook Ventures: https://www.overlook.vc | https://www.linkedin.com/company/overlookvc/

👤 Hosts:

James Benham: https://www.linkedin.com/in/jbenham

Rob Galbraith: https://www.linkedin.com/in/rob-galbraith/

🎙️ This episode is sponsored by Terra — the next-generation Workers' Comp and Commercial P&C Software.

Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/

📌 Find InsurTech Geek:

LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/

Twitter/X: https://twitter.com/InsurtechGeek

Instagram: https://www.instagram.com/insurtechgeek/

Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓